In a fact WELL known to Leafs fans, the Toronto Maple Leafs have not won a Stanley Cup since 1967, and there are two key culprits. They are ineffective at converting draft picks into quality NHL players, and they are often on the losing end of trades. They often squander assets either by failing to utilize draft picks they receive, or by acquiring declining assets (aging veterans) for assets that are not yet at their peak (prospects). After identifying a few trades that were bad, but not quite bad enough, we will look at the trades that ranked #21-25 among the Worst Maple Leafs trades of all time.

Dis-Honourable Mention: Toronto trades Adam Mair and a 2nd Round Pick in 2001 (Mike Cammalleri) to the Los Angeles Kinds for Aki Berg (March 13th, 2001)
A former first-round pick, Aki Berg was a large player with a small presence, and especially loathed by Toronto fans. Adam Mair didn’t do much in Los Angeles, playing just 28 games. But he found his footing as a depth forward, playing over 500 games since leaving the Kings. L.A. also struck gold by picking Cammalleri, but a straight Mair-for-Berg swap is already a dud for Toronto. Bad, but not awful.

Dis-Honourable Mention: Toronto trades Damian Rhodes and Ken Belanger to the New York Islanders for Don Beaupre and Kirk Muller (January 23rd, 1996)
Toronto moved Damien Rhodes amid talk that Rhodes was too good to simply be a back-up to Felix Potvin. They haven’t had a solid back-up keeper since. Beaupre was a putrid 0-8-0 in 11 games over parts of two seasons, with a 4.84 GAA and a .843 save percentage. Muller was decent, but past his best-before date as a top-flight forward: he put up 62 points in 102 games before being shipped to Florida for Jason Podollan. Ugh. Meanwhile, Rhodes played 262 games for Ottawa and Atlanta, putting up decent numbers (2.87 GAA, .897 save %) despite playing for weak teams (79-122-43 record).

Dis-Honourable Mention: Toronto Carlo Coliacovo and Alexander Steen to the St. Louis Blues for Lee Stempniak (November 24th, 2008)
Acquired by Cliff Fletcher just a few days before Brian Burke’s arrival, Stempniak’s reputation was defined by a 27-goal, 52-point season in ’06-07 for the Blues. But he barely eclipsed those totals in 123 games as a Leaf before being dealt to Phoenix. Meanwhile, Steen has become a decent forward in St. Louis, twice clearing 20 goals in four seasons. And Coliacovo was strong on the blueline for St. Louis, scoring 26+ points for three consecutive seasons. So the Leafs traded two reliable-if-unspectacular players who are still young four years later for parts of two seasons from a one-hit wonder. To make matters worse, Steen was rumoured to be the centerpiece of the Blues’ requested package (along with Tomas Kaberle) during Chris Pronger trade talks after the ’04-05 NHL lockout. However, the Leafs REFUSED to part with Steen, and the Blues ended up trading Pronger to Edmonton. But who needs Chirs Pronger, when you can have Lee Stempniak?

Dis-Honourable Mention: Toronto trades Dave Andreychuk to the New Jersey Devils for a 2nd Round Pick in 1996 (Marek Posmyk) and a 3rd Round Pick in 1999 (later traded back to NJ, who selected Andre Lakos) (March 13th, 1996)
With the Leafs struggling during the ’95-96 season, Andreychuk was deemed either too expensive or no longer a fit. Likely the first one, knowing the reputation of Leafs’ ownership under Steve Stavro. Andreychuk was dealt for a pair of picks, one of which ended up going back to New Jersey a year later in the Gilmour trade, while Posmyk never played for Toronto and only suited up for 19 career NHL games. Andreychuk meanwhile played well for Jersey before his play tailed off. But he still posted four consecutive 20+ goal seasons from ’00-01 to ’03-04, and won a Stanley Cup as the captain of the Tampa Bay Lightning nearly a decade after being deemed a spare part on the Leafs.

So those are the trades that, while awful, weren’t bad enough to make the “Worst Of” list. And with that, I present the Trades #21-25 on the list of Worst Maple Leafs Trades of the Modern Era.

#25: Toronto trades Ken Wregget to the Philadelphia Flyers for a 1st Round Pick in 1989 (Rob Pearson) and a 1st Round Pick in 1989 (Steve Bancroft) (March 6th, 1989)
In 1989, the Leafs had a pair of young goaltenders: Ken Wregget and Allan Bester. As is traditional in Toronto, when presented with an opportunity to choose between two goaltenders, we chose the wrong one (please refer to the case of Pogge v. Rask for a more recent example). I’m not sure as to Philadelphia’s motivation, but the Flyers were likely looking to add a goaltender to back up Ron Hextall. I can’t say I blame Leafs management for making this trade; they had a pair of 25-year-old goalies, and the Flyers were offering a pair of first-round picks for one of them. Unfortunately, Bester was merely an average goalie on a terrible defensive hockey team. He started 42 games in 1989-90, and in 1990-91 he played just six games before being dealt to Detroit. He was replaced by the tandem of Peter Ing and Jeff Reese, until Cliff Fletcher paid a steep price (including Vincent Damphousse) to acquire Grant Fuhr before the ’91-92 season. This isn’t to say that Wregget would have been able to get the Leafs to the next level where Bester failed, but the fact remains that Bester played just 20 NHL games after 1989-90, and he was out of the NHL by 1996. Wregget meanwhile won a Stanley Cup with Pittsburgh in 1992, and posted strong numbers right up until his retirement.

The Leafs now found themselves with three first round selections in the 1989 NHL Entry Draft, and this was at a time when there were just 21 teams in the NHL. And for some reason, the Leafs decided to use all three selections on the SAME OHL team, choosing Scott Thornton, Rob Pearson and Steve Bancroft from the Belleville Bulls. Someone needs to ask Gord Stellick about that one. Thornton had a very respectable career, playing 941 games… but just 33 were for Toronto. And while Pearson was a member of the ’93 and ’94 Leafs, he was hardly an impact player; he scored more than 20 goals just once, and had 6 points in 33 career playoff games. Bancroft was a complete waste of a pick, playing just six NHL games.

The 1989 draft wasn’t a particularly deep one (except for Detroit), but Toronto’s selections were still terrible. Steven Rice and Jamie Heward were first-rounders that became marginal NHLers, but even they had more points than Pearson. And no disrespect to Thornton (285 points), but he was selected ahead of Stu Barnes (597 points), Bill Guerin (429 goals), Bobby Holik (747 points) and Mike Sillinger (548 points), all of whom played 1,000+ NHL games. Meanwhile, Olaf Kolzig and Kevin Haller (600-700 games each) were chosen after Pearson. And those players were all chosen in the first round. The only picks worse than Bancroft were Jason Herter (VAN, one NHL game) and Jason Soules (EDM, zero NHL games).

Toronto made some terrible draft picks, squandering what they received for Wregget. It took them three years to recover in net from this trade. So while Wregget likely wouldn’t have been a game-changer for Toronto, and there weren’t any real slam-dunks in the first round after Mats Sundin, this trade still stinks.

#24: Toronto trades Alyn McCauley, Brad Boyes and a 2003 1st Round Pick (later traded to Boston, who selected Mark Stuart) to the San Jose Sharks for Owen Nolan (March 5th, 2003)
This is a trade still reviled by Leafs fans, and representative of the team’s failed strategy during the mid-2000’s of bringing in anyone and everyone of name value (see also Phil Housley, Brian Leetch, Ron Francis and one shift from Doug Gilmour). Nolan did well down the stretch in ’02-03, but flopped in the playoffs, recording zero goals and two assists in the Leafs’ first-round loss. His brief Leafs’ career ended with 26 goals and 60 points in 79 games over two seasons: decent enough stats for a single season, but not for an entire run, especially when it failed to boost the Leafs’ playoff fortunes one iota. As a fan, losing McCauley (hero of the incredibly fun 2002 playoff run) sucked. From a numbers perspective, he played 174 games over parts of three seasons with the Sharks, posting a respectable 83 points (half of his career total) as a solid two-way forward. Brad Boyes only played one game with the Sharks, before developing into a decent scorer with Boston and St. Louis. He posted three 60+ point seasons, and scored 43 goals for the Blues in the ’07-08 season. Finally, Mark Stuart was a bust, never even playing for San Jose.

The acquisition of Owen Nolan was heralded as the “right move” by fans and media alike in 2003, because of his reputation for leadership and strong play in the clutch. Instead he failed to impact the team, and had a bitter departure from the Leafs due to injury lawsuits. To add insult to injury (pun intended), he continued to be a useful NHLer post-Toronto, scoring 150 points in 285 games for Phoenix, Calgary and Minnesota over four seasons.

On a side note, it is intensely depressing that Boyes was the first NHLer drafted by Toronto to get 40 goals in a season since Wendel Clark, who was drafted way back in 1985. To be COMPLETELY clear, I did NOT say that Boyes was the first to score 40 goals as a Leaf; he was the first (and as of 2013, ONLY) Toronto draftee to score 40 goals for ANY NHL team since Clark.

#23: As compensation for signing Mike Craig as a Restricted Free Agent (July 29th, 1994), Toronto sends Peter Zezel and Grant Marshall to the Dallas Stars (August 10th, 1994) When I created this list the first time, I ranked this deal way too high. But it wasn’t because the Leafs gave up so much; it was because I loathed Mike Craig as the worst Maple Leaf acquisition in history (in my opinion). The reality is he was terrible, and far from worth the price, but there are many deals more damaging to the Maple Leaf franchise.

That being said, I HATED Mike Craig as a Leaf. I strongly disliked him in Minnesota, and I LOATHED him in Toronto. I’m not even 100% why; just watching him and his curly mullet on the ice made me want to throw my shoe at him. Craig was a 15-goal, 30-point scorer that the Leafs felt absolutely compelled to sign to an offer when he became a Restricted Free Agent. To be fair, Craig was a 20-goal scorer for Toronto… unfortunately, it took him 172 games to score those 20 goals. Yup… 20 goals and 50 points over three seasons, along with a lone assist in eight playoff games. Did I mention that I hated him?

Beyond Craig’s lack of contribution, the compensation package the Leafs gave up was absolutely brutal. Peter Zezel was a competent checking centre, and as part of the BOZ (Berg, Osborne, Zezel) line gave Toronto a grind/energy line that was incredibly efficient during the ’93 and ’94 runs to the Conference Final. Unfortunately, Zezel went to Dallas, and the Leafs lacked a true checking line for a long time. The Leafs also lost prospect Grant Marshall, who was their first-round pick in 1992. He played 402 games with Dallas, recording 134 points as a decent two-way player. After leaving the Stars organization, he played another 298 games (and recorded another 105 points). And on top of that, he won a pair of Stanley Cups; one with Dallas, and one with New Jersey. To summarize, the Leafs gave up on another few seasons of Peter Zezel (211 post-Toronto games) and a 700-game career from a two-time Cup-winning grinder for Mike f-ing Craig. And the terrible part is, it could have been worse; the Stars wanted blue-chip Leafs prospect Kenny Jonsson, while the Leafs countered with Zezel and Marshall. Fortunately, the arbiter sided with Toronto. Unfortunately, Fletcher made a huge mistake signing Craig in the first place, and trading Jonsson later on (coming up later on this list).

#22: Toronto trades Laurie Boschman to the Edmonton Oilers for Walt Poddubny and Phil Drouillars (March 9th, 1982) I will freely admit, Laurie Boschman isn’t exactly a renowned ex-Leaf, and only played parts of three seasons here. And he doesn’t spring to mind for many when talking about regrettable losses from Leafland. But his career numbers demonstrate that the Leafs made a mistake in letting him go. Boschman’s stats weren’t overwhelming in Toronto, and some internal issues (like Leafs’ owner Harold Ballard suggesting Boschman’s Christianity made him play poorly) resulted in him being dealt to the Oilers. Walt Poddubny had a decent first full season as a Leaf, scoring 28 goals and 59 points in 1982-83. But then injuries limited him to just 103 games over the next three seasons (although he did tally a respectable 79 points). But after the Leafs gave up on him and dealt him to the New York Rangers, he contributed seasons of 40 and 38 goals, followed by another 38-goal performance in Quebec. In return, the Leafs received Mike Allison, who gave them 26 points over 86 games. Huzzah. The other player from the Boschman trade, Phil Drouillars, never played in the NHL.

Now Boschman didn’t exactly light the world on fire in Edmonton; he recorded just 25 points in 73 games. But the Oilers then dealt Boschman to the Winnipeg Jets, where he finally found his niche. Over a 5-year period from 83-84 to 87-88, Boschman averaged 26 goals, 62 points and 207 penalty minutes. That production would have placed him in the Top 4 in Leafs’ scoring every season during that period. After a few more seasons with Winnipeg and New Jersey, Boschman eventually retired after spending the 1992-93 season as the first-ever captain of the Ottawa Senators. He finished his career with 1,009 games played, and is one of a small group of players with at least 500 points and 2,000 penalty minutes in NHL history.

#21: Toronto trades a 1st Round Pick in 2007 (later traded to St. Louis, who selected Lars Eller), a 2nd Round Pick in 2007 (later traded to St. Louis, who selected Aaron Palushaj) and a 4th Round Pick in 2009 (later traded to Nashville, who selected Craig Smith) to the San Jose Sharks for Vesa Toskala and Mark Bell (June 22nd, 2007)This deal came about after the Leafs missed the 2007 playoffs with Andrew Raycroft in net (a deal which we’ll discuss later). Ex-Leafs’ GM John Ferguson Jr. compounded that mistake by acquiring Vesa Toskala from the Sharks. The reasoning was that Miikka Kiprusoff had been buried in the Sharks’ system, and turned out to be a hidden gem of an all-star. Furthermore, the Toronto media touted how the Flames originally wanted Toskala, but “settled” on Kiprusoff. By that reasoning, Toskala would be even BETTER than the man who took the Flames to the Finals in 2004, and then won Vezina and Jennings as a First-Team All-Star in 2006. Oh if only that were true.

The Sharks flipped the 1st and 2nd rounders along with a 3rd rounder in 2008 to St. Louis in order to jump up from 13th to 9th, which they used to select Logan Couture. Couture is a rising star in the NHL, posting back-to-back 30-goal seasons in ’10-11 and ’11-12 before he turned 23. The Blues then selected Lars Eller, whom they later dealt to Montreal as part of the Jaroslav Halak trade. On a side note, it’s fantastic to see a deal that pains Leafs’ fans can ALSO be linked to a deal that pains Habs fans. And the linkage intensified when Palushaj was dealt by the Blues to Montreal in a separate deal. Now I mentioned earlier that I don’t consider who the opposing team drafts: but there were a number of highly-touted players picked after Couture (including Brandon Sutter, Ryan McDonagh, Max Pacioretty and David Perron) in the first round of the 2007 draft. The Leafs would have had plenty of quality players to choose from in a fairly deep draft.

That covers the outgoing side. What of the incoming? Well, Mark Bell was suspended 15 games for a DUI conviction (as reported by TSN) before even setting foot onto the ice as a Leaf. And when he did, the results were underwhelming: 4 goals and 10 points in 35 games. He was demoted in October of 2008 to the Marlies, and then claimed on re-entry waivers by the Rangers. He didn’t play in the NHL again until he dressed for five games with Anaheim in the 2011-12 season. And Toskala… wow, where to begin? The man was injury-prone and maddeningly inconsistent. If you search “Toskala 197 Foot Goal” on YouTube, you get 15 links to the infamous goal he let in against the Islanders in March 2008. Try “Toskala Goal Sabers” for beautiful footage of a terrible floater from the blueline that went off his glove and in against Buffalo in December 2009. To make matters worse, the Leafs signed Toskala to a contract extension before he even put on a Leafs jersey… and when his 2007-2008 season didn’t exactly pan out, his contract quickly became dead weight in the Salary Cap era. Thankfully, ex-Leafs GM Brian Burke managed to unload Toskala (and Jason Blake, one of the worst free-agent signings of the JFJ era) onto Burke’s former employers in Anaheim. The Ducks then dumped Toskala in Calgary, briefly reuniting him with former Sharks’ teammate Kiprusoff and seemingly half of the 2009 Leafs (i.e. Stajan, Hagman, Myers and White).

So looking at the big picture involving the Sharks, Blues and Leafs: San Jose has a young stud centre (which the Leafs are lacking), the Blues have an all-star goalie (which the Leafs are also lacking), and the Leafs got 145 games of Vesa Toskala and 48 games of J-S Giguere. Plus the Leafs now have absolutely nothing to show for the trade, as Giguere left for Colorado as a free agent. It almost makes me think that Ferguson’s current employment with the Sharks was a reward for his role in this deal. Almost… except I sincerely doubt Ferguson has foresight of any kind. If trading for Raycroft was like betting your rent money at the craps table, then trading for Toskala was like betting NEXT month’s rent money immediately afterwards, and Vesa’s contract extension was like throwing in your car keys.

We are now on the road to examining some key reasons for the downfall of the Toronto Maple Leafs. If you have a weak stomach, I advise you to turn back now! But for those of you who can take it, or for those Leafs fans who want to take an extremely depressing trip down memory lane, check out the trades that ranked #16-20.

I poorly worded that statement: I meant that he was a bust for San Jose since he never suited up for them. But your point is valid; bust is too strong a word. Stuart he’s become a capable NHL regular over the past 5-6 seasons.